Author: Jessica.F

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., name: 2-Oxoindoline-5-carboxylic Acid

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 118289-55-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 3. 5-(2-(4-Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride. (I); A reactor is loaded with 131 g (0.57 mol) of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-indol-2-one, 125 g (0.57 mol) of piperazinyl benzoisothiazole, 260 ml of dimethylsulfoxide, 26 ml of water and 4.3 g (0.0285 mols) ofNaI. The reaction mixture is added with 103 g (0.969 mol) of Na2CO3, with stirring under nitrogen atmosphere. The resulting mixture is heated to about 115-125C in 1 h and kept at said temperature under stirring for approx. 1 hr 45 min, then cooled and slowly added in about 25 min with isopropyl alcohol (650 ml), at a temperature of about 110C, then slowly cooled at 25C. The filtrate and the precipitate are washed with isopropyl alcohol (2 x 130 ml) to obtain 310 g of 5-(2-(4-benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one free base, as a crystalline solid. The resulting product is placed in a 3 L beaker with 1500 ml of purified water, and 150 ml of 32% HCl are dropped therein with stirring. The reaction mixture is kept under stirring for 10 min, filtered, washed with purified water (2 x 500), dried to give 260 g of 5-(2-(4-benzo[d]isothiazol-3-yl)piperazin-1-yl) ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride, as a crystalline solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dipharma S.p.A.; LUNDBECK PHARMACEUTICALS ITALY S.p.A.; EP1787990; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 193354-13-1,Some common heterocyclic compound, 193354-13-1, name is 5-Iodoindolin-2-one, molecular formula is C8H6INO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1. Synthesis of 5-Methoxycarbonyl-2-oxindole. 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.15 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on a silica gel in 30% ethyl acetate in hexane. The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

The synthetic route of 193354-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 32692-19-6, Computed Properties of C8H8N2O2

General procedure: A solution of indoline (20) (1.88 mL, 16.78 mmol), tert-butyl 3-oxopyrrolidine-1-carboxylate (22) (3.73 g, 20.13 mmol) in dry methanol (20 mL) was treated with AcOH (2.37 mL, 41.95 mmol) followed by NaCNBH3 (1.26 g, 20.13 mmol) at 0 C. ;The reaction was brought to room temperature and stirred for 3 h. ;The reaction was basified with 1 N NaOH solution and product was extracted into CH2Cl2. ;The combined CH2Cl2 layer was dried (Na2SO4) and solvent was evaporated to obtain crude product. ;The crude was purified by column chromatography (EtOAc:hexanes, 1:9) to obtain the title compound

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 317-20-4

General procedure: The mixture of isatin 1 (58.9 mg, 0.4 mmol), antipyrine 2 (37.6 mg, 0.2 mmol) andimidazole (20 mol %, 0.04 mmol) in 1 mL H2O were stirred at 80 . Once thereaction completed, the solid mixture was filtered, washed by water and dried undervacuum to afford the analytically pure products 3. In some cases, the desired pureproducts were obtained by silica gel chromatography using ethyl acetate as eluent.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yong; Nie, Long-Jun; Luo, Liang; Mao, Jia-Xin; Liu, Jin-Xiang; Xu, Guo-Hai; Chen, Deliang; Luo, Hai-Qing; Tetrahedron; vol. 76; 7; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1504-06-9, name is 3-Methyloxindole, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 1504-06-9

A magnetic stirrer was added to the Schlenk tube-sealed reactor, and the 2- oxindole compound of formula II-1 (0.3 mmol) was added, followed by the addition of Cu (OAc) 2 (0.03 mmol) and di-tert-butyl peroxide. (0.6mmol); The reactor was then placed in an oil bath equipped with magnetic stirring, and the reaction was heated and stirred at 120 C for 4 hours. The reaction mixture was completely monitored by TLC. After the completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue was separated by column chromatography (eluent solvent: ethyl acetate / n-hexane) to obtain he title compound formula I-1 , yield 80%.

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ningbo University; Bao Wenhui; Wei Wenting; Gao Lehan; Wang Xinye; (11 pag.)CN108129378; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, A new synthetic method of this compound is introduced below., name: 1-(2,6-Dichlorophenyl)-2-indolinone

Example 1Step a) of preparation of sodium diclofenacIn a four-necked glass flask the following ingredients were charged:- 1 -(2,6-dichlorophenyl)-2-indolinone g 592 (M.W. 278.13 moles: 2.128)- Water cc 2368- Sodium hydrosulfite g 40- Sodium hydroxide 30 % g 851 (M.W.: 40; moles: 6.38)The mixture was refluxed for 6 hours, then cooled to 35 – 37 C. The precipitate was filtered on buchner funnel, then washed with water (cc 1600) preheated to 35- 37 C. Wet 1016 grams of sodium diclofenac were obtained corresponding to dry 625 grams (Theor. g 677.1 )

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; COSMA S.P.A.; IBSA INSTITUT BIOCHIMIQUE S.A.; AVOGADRI, Alvaro; LUSSANA, Massimiliano; PIZZATTI, Enrica; BARETTI, Sergio; WO2010/69397; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1504-06-9, name is 3-Methyloxindole, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1504-06-9, category: indolines-derivatives

Step 1 : Preparation of 3-methyl-5-(3-trifluoromethylphenyl)- 1 ,3-dihydroindol-2-oneA solution of 3-methyloxindole (5.06 g, 34.4 mmol) in iV,iV-dimethylformamide (60 mL) was cooled to 0 0C. N-Bromosuccinimide (6.23 g, 35.0 mmol) was added, and the resulting solution was stirred for 18 hours while slowly warming to room temperature. The reaction was then diluted with ethyl acetate (100 mL) and washed with 1 :1 saturated aqueous NaCl solutuion:H2O (3 x 75 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated under reduced pressure to give a solid that was used without further purification in the next step described below.A mixture of the crude product described above (1.02 g5 4.51 mmol), 3- (trifluoromethyl)phenylboronic acid (0.983 g, 5.18 mmol), sodium carbonate (0.884 g, 8.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.252 g, 0.218 mmol) in ethylene glyclol dimethyl ether (8.0 mL) and H2O (1.0 mL) was warmed to 80 0C. After 20 hours, the mixture was cooled to room temperature, poured into 1 : 1 saturated aqueous NaCl solution:H2O (50 mL), and extracted with ethyl acetate (3 x 50 mL). The organic extracts were combined, dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage 4OM, eluting with 10-35% ethyl acetate/hexanes, to give 3-methyl-5-(3-trifluoromethylphenyl)-l,3-dihydroindol-2-one as a white solid.1H NMR (CDCl3): delta 8.27 (br s, 1 H), 7.79 (s, 1 H), 7.72 (d, I H1 J = 7.3 Hz), 7.56 (m, 2 H), 7.46 (m, 2 H), 6.99 (m, 1 H), 3.55 (dd, 1 H, J = 15.3, 7.8 Hz), 1.57 (d, 3 H, J = 7.7 Hz) MS: m/e 292.41 (M + H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyloxindole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 201940-08-1,Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a suspension of tert-butyl 5-bromo-2-(tert-butoxycarbonyl)isoindoline (1.2 g, 4 mmol) and bis(pinacolato)diboron (2 g, 8 mmol) in DMSO (20 mL) was added AcOK (1.6 g, 16 mmol), followed by Pd(dppf)Cl2-CH2Cl2 (327 mg, 0.4 mmol) under N2 atmosphere. The reaction was heated at 90 C for 12 h, then cooled to rt and poured into EtOAc/H20 (300 mL/100 mL). The separatedorganic phase was washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) =20/1) to give the title compound as yellow oil (1 g, 73%). MS (ESI, pos. ion) m/z: 290.2 [M-56+l ; NMR (400 MHz, CDC13) delta (ppm): 7.68-7.74 (m, 2H), 7.23-7.30 (m, 1H), 4.64-4.70 (m, 4H), 1.53 (s, 9H), 1.36 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 5-bromoisoindoline-2-carboxylate, its application will become more common.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18711-13-2, Computed Properties of C8H3Cl2NO2

General procedure: To a stirred solution of ethyl 2-(triphenylphosphoranylidene)acetate (3.83 g, 11.0 mmol) in CH2Cl2 (30.0 mL) was added isatin (1.47 g, 10.0 mmol) at 0 C. After stirring for 8 h at 0 C, the mixture was concentrated by rotary evaporation. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=3:1-10:1) to afford the compound 1a as a red solid (1.78 g, 82 %).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Zhao, Jia; Guan, Shuicheng; Zhou, Xiaojian; Han, Wenyong; Cui, Baodong; Chen, Yongzheng; Tetrahedron; vol. 72; 22; (2016); p. 3098 – 3104;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem